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F6562

Sigma-Aldrich

Fmoc-(R)-2-(7-octenyl)Ala-OH

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Synonym(s):
(R)-N-Fmoc-α-(7-Octenyl)alanine, Fmoc-(R)-2-(7-octenyl)alanine, Fmoc-(R)-2-amino-2-methyl-dec-6-enoic acid
Empirical Formula (Hill Notation):
C26H31NO4
CAS Number:
Molecular Weight:
421.53
MDL number:
PubChem Substance ID:
NACRES:
NA.26

form

solid

Quality Level

reaction suitability

reaction type: Fmoc solid-phase peptide synthesis

application(s)

peptide synthesis

functional group

Fmoc

storage temp.

−20°C

SMILES string

O=C(OCC1C(C=CC=C2)=C2C3=C1C=CC=C3)N[C@@](CCCCCCC=C)(C)C(O)=O

InChI

1S/C26H31NO4/c1-3-4-5-6-7-12-17-26(2,24(28)29)27-25(30)31-18-23-21-15-10-8-13-19(21)20-14-9-11-16-22(20)23/h3,8-11,13-16,23H,1,4-7,12,17-18H2,2H3,(H,27,30)(H,28,29)/t26-/m1/s1

InChI key

MADFVGMQNXRFAF-AREMUKBSSA-N

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This Item
F6687F6187F6437
Fmoc-(R)-2-(7-octenyl)Ala-OH

F6562

Fmoc-(R)-2-(7-octenyl)Ala-OH

Fmoc-(S)-2-(7-octenyl)Ala-OH ≥97%

F6687

Fmoc-(S)-2-(7-octenyl)Ala-OH

Fmoc-(R)-2-(2-propenyl)Ala-OH ≥97%

F6187

Fmoc-(R)-2-(2-propenyl)Ala-OH

Fmoc-(R)-2-(pentenyl)Ala-OH ≥97% (HPLC)

F6437

Fmoc-(R)-2-(pentenyl)Ala-OH

functional group

Fmoc

functional group

Fmoc

functional group

Fmoc

functional group

Fmoc

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

reaction suitability

reaction type: Fmoc solid-phase peptide synthesis

reaction suitability

reaction type: Fmoc solid-phase peptide synthesis

reaction suitability

reaction type: Fmoc solid-phase peptide synthesis

reaction suitability

reaction type: Fmoc solid-phase peptide synthesis

application(s)

peptide synthesis

application(s)

peptide synthesis

application(s)

peptide synthesis

application(s)

peptide synthesis

Application

Olefinic alpha-methyl amino acid for peptide stapling. Upon incorporation of this amino acid into a peptide, along with another of the same or derivative with a different length of the olefinic side chain, the two can be ′stapled′ via a ring closing metathesis reaction with Grubb′s catalyst (product # 579726). The resulting stapled peptide macrocycle has been shown to stabilize the alpha-helical structure of peptides, which can lead to favorable biological characteristics such as increased proteolytic stability and cellular uptake.

pictograms

Environment

signalword

Warning

hcodes

Hazard Classifications

Aquatic Acute 1

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


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Young-Woo Kim et al.
Nature protocols, 6(6), 761-771 (2011-06-04)
This protocol provides a detailed procedure for the preparation of stapled α-helical peptides, which have proven their potential as useful molecular probes and as next-generation therapeutics. Two crucial features of this protocol are (i) the construction of peptide substrates containing
Ban Xiong Tan et al.
Scientific reports, 5, 12116-12116 (2015-07-15)
Previous publications on stapled peptide inhibitors against Mdm2/Mdm4-p53 interactions have established that this new class of drugs have the potential to be easily optimised to attain high binding affinity and specificity, but the mechanisms controlling their cellular uptake and target

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